Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E
Name
synthesis-of-kopsifoline-a-and-kopsifoline-e.pdf
Description
Submitted version
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701.68 KB
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Unknown
Checksum (MD5)
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Author(s)
Myeong, In-Soo
Avci, Nadide Hazal
Movassaghi, Mohammad
Alternative Title
Total Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E
Date Issued
2021
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Myeong, In-Soo, Avci, Nadide Hazal and Movassaghi, Mohammad. 2021. "Total Synthesis of (−)-Kopsifoline A and (+)-Kopsifoline E." Organic Letters, 23 (23).
Version
Original manuscript
Abstract
We report the first total synthesis of (-)-kopsifoline A and (+)-kopsifoline E. Our synthetic strategy features a biogenetically inspired regioselective C17-functionalization of a versatile intermediate containing the pentacyclic core of aspidosperma alkaloids. The vinylogous urethane substructure of this intermediate affords (-)-kopsifoline D via C3-C21 bond formation under the Mitsunobu reaction conditions, while it enables selective C17-functionalization en route to (-)-kopsifoline A and (+)-kopsifoline E.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/acs.orglett.1c03448
